
Luxury Apartments for Rent in Chestertown, MD (18 Rentals)
The most luxurious Apartments in Chestertown with high-end amenities, features, and finishes.


Arbors Greenleigh
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

3200 Wilson Ave

14073 Augustine Herman Hwy

188 Joppa Farm Rd

534 Calvert Way

101 Trails Way

25 Queen Elizabeth Ct

2144 Firethorn Rd

126 Price St
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

102 Long Dr

1920 Sue Ave

137 Warbler Wy

6505 Totteridge St

137 Warbler Wy

311 Brick Schoolhouse Rd
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
Chestertown, MD Local Guide

How much does it cost to rent an apartment in Chestertown?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Chestertown Studio Apartments | $1,338 | $899 | $1,699 |
Chestertown 1 Bedroom Apartments | $1,530 | $946 | $2,266 |
Chestertown 2 Bedroom Apartments | $1,772 | $1,039 | $2,900 |
Chestertown 3 Bedroom Apartments | $2,016 | $1,285 | $3,209 |
Chestertown 4 Bedroom Apartments | $2,166 | $1,969 | $2,245 |
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Chestertown, MD Local Guide
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Getting Around Chestertown, MD
Walk Score®
47 / 100
Car-Dependent
Most errands require a car
Bike Score®
55 / 100
Bikeable
Some bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about Chestertown
How much are Studio apartments in Chestertown?
There are currently 6 Studio Apartments in Chestertown with rent ranges from $899 to $1,699 with an average price of $1,338.
What is the current price range for One Bedroom Chestertown Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Chestertown ranges from $946 to $2,266 with an average monthly rent of $1,530.
What does renting a Two Bedroom Apartment in Chestertown cost?
The monthly rent prices of Two Bedroom Apartments currently available in Chestertown range from $1,039 to $2,900. Today's average rental price for Two Bedrooms here is $1,772.
How expensive are Chestertown Three Bedroom Apartments?
There are currently 28 Three Bedroom Apartments listings available in Chestertown on ApartmentHomeLiving.com. The pricing ranges from $1,285 to $3,209 - averaging $2,016 for the location.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.